2′-fluoro RNA shows increased watson-crick H-bonding strength and stacking relative to RNA: Evidence from NMR and thermodynamic Data

Angewandte Chemie - International Edition

Volumn 51, Issue 47, 2012, Pages 11863-11866

  Patra, Amritraj ^a   Paolillo, Michael ^b   Charisse, Klaus ^c   Manoharan, Muthiah ^c   Rozners, Eriks ^b   Egli, Martin ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b BINGHAMTON UNIVERSITY   (United States)

^c ALNYLAM PHARMACEUTICALS   (United States)

Author keywords

2 FRNA; hydrogen bonding; NMR spectroscopy; RNA; thermodynamics

Indexed keywords

BASE STACKING; DUPLEX STABILITY; H-BONDING; OSMOTIC STRESS; RNA DUPLEXES; THERMODYNAMIC DATA; UV MELTING;

DIFFUSION BONDING; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; THERMODYNAMICS;

RNA;

RNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS;

HYDROGEN BONDING; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; RNA; THERMODYNAMICS;

EID: 84869391995     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204946     Document Type: Article

References (36)

1. W. A. Pieken, D. B. Olsen, F. Benseler, H. Aurup, F. Eckstein, Science 1991, 253, 314-317.
2. A. M. Kawasaki, M. D. Casper, S. M. Freier, E. A. Lesnik, M. C. Zounes, L. L. Cummins, C. Gonzalez, P. DanCook, J. Med. Chem. 1993, 36, 831-841.
3. M. Egli, P. S. Pallan, C. Allerson, T. Prakash, A. Berdeja, J. Yu, S. Lee, A. Watt, H. Gaus, B. Bhat, E. Swayze, P. Seth, J. Am. Chem. Soc. 2011, 133, 16442-16449.
4. C. R. Allerson, N. Sioufi, R. Jarres, T. P. Prakash, N. Naik, A. Berdeja, L. Wanders, R. H. Griffey, E. E. Swayze, B. Bhat, J. Med. Chem. 2005, 48, 901-904.
5. M. Manoharan, A. Akinc, R. K. Pandey, J. Qin, P. Hadwiger, M. John, K. Mills, K. Charisse, M. A. Maier, L. Nechev, E. M. Greene, P. S. Pallan, E. Rozners, K. G. Rajeev, M. Egli, Angew. Chem. 2011, 123, 2332-2336
6. Angew. Chem. Int. Ed. 2011, 50, 2284-2288.
7. S. Davis, S. Propp, S. M. Freier, L. E. Jones, M. J. Serra, G. Kinberger, B. Bhat, E. E. Swayze, C. F. Bennett, C. Esau, Nucleic Acids Res. 2009, 37, 70-77.
8. E. W. M. Ng, D. T. Shima, P. Calias, E. T. Cunningham, D. R. Guyer, A. P. Adamis, Nat. Rev. Drug Discovery 2006, 5, 123-132.
9. F. Rigo, Y. Hua, S. J. Chun, T. P. Prakash, A. R. Krainer, F. Bennett, Nat. Chem. Biol. 2012, 8, 555-561.
10. P. S. Pallan, E. M. Greene, P. A. Jicman, R. K. Pandey, M. Manoharan, E. Rozners, M. Egli, Nucleic Acids Res. 2011, 39, 3482-3495.
11. M. Egli, S. Portmann, N. Usman, Biochemistry 1996, 35, 8489-8494.
12. A. J. Dingley, J. E. Masse, R. D. Peterson, M. Barfield, J. Feigon, S. Grzesiek, J. Am. Chem. Soc. 1999, 121, 6019-6027.
13. S. S. Wijmenga, M. Kruithof, C. W. Hilbers, J. Biomol. NMR 1997, 10, 337-350.
14. J. Czernek, R. Fiala, V. Sklenar, J. Magn. Reson. 2000, 145, 142-146.
15. M. Barfield, A. J. Dingley, J. Feigon, S. Grzesiek, J. Am. Chem. Soc. 2001, 123, 4014-4022.
16. M. N. Manalo, X. Kong, A. LiWang, J. Am. Chem. Soc. 2005, 127, 17974-17975.
17. M. Swart, C. F. Guerra, F. M. Bickelhaupt, J. Am. Chem. Soc. 2004, 126, 16718-16719.
18. rd ed., (Eds.: G.M. Blackburn, M.J. Gait, D. Loakes, D.M. Williams,), Royal Society of Chemistry, Cambridge, UK, 2006, pp. 13-75.
19. I. Vakonakis, A. C. LiWang, J. Am. Chem. Soc. 2004, 126, 5688-5689.
20. I. Vakonakis, A. C. LiWang, J. Biomol. NMR 2004, 29, 65-72.
21. B. Reif, V. Wittmann, H. Schwalbe, C. Griesinger, K. Wörner, K. Jahn-Hofmann, J. W. Engels, W. Bermel, Helv. Chim. Acta 1997, 80, 1952-1971.
22. S. M. Freier, R. Kierzek, J. A. Jaeger, N. Sugimoto, M. H. Caruthers, T. Neilson, D. H. Turner, Proc. Natl. Acad. Sci. USA 1986, 83, 9373-9377.
23. K. Guckian, B. A. Schweitzer, R. X.-F. Ren, C. J. Sheils, P. L. Paris, D. C. Tahmassebi, E. T. Kool, J. Am. Chem. Soc. 1996, 118, 8182-8183.
24. R. Micura, M. Bolli, N. Windhab, A. Eschenmoser, Angew. Chem. 1997, 109, 899-902
25. Angew. Chem. Int. Ed. Engl. 1997, 36, 870-873.
26. P. S. Pallan, P. Lubini, M. Bolli, M. Egli, Nucleic Acids Res. 2007, 35, 6611-6624.
27. K. J. Breslauer, Methods Enzymol. 1995, 259, 221-242.
28. C. H. Spink, J. B. Chaires, Biochemistry 1999, 38, 496-508.
29. E. Rozners, J. Moulder, Nucleic Acids Res. 2004, 32, 248-254.
30. E. Rozners, Curr. Protoc. Nucleic Acid Chem. 2010, 43, 7.14.1- 7.14.13.
31. P. L. Vanegas, G. A. Hudson, A. R. Davis, S. C. Kelly, C. C. Kirkpatrick, B. M. Znosko, Nucleic Acids Res. 2012, 40, D 439 -D 444
32. http://cossmos.slu.edu.
33. D. G. Sashital, V. Venditti, C. G. Angers, G. Cornilescu, S. E. Butcher, RNA 2007, 13, 328-338.
34. J. P. Sheehy, A. R. Davis, B. M. Znosko, RNA 2010, 16, 417-429.
35. M. N. Manalo, L. M. Pérez, A. LiWang, J. Am. Chem. Soc. 2007, 129, 11298-11299.
36. P. P. Seth, J. Yu, A. Jazayeri, P. S. Pallan, C. R. Allerson, M. E. Ostergaard, F. Liu, P. Herdewijn, M. Egli, E. E. Swayze, J. Org. Chem. 2012, 77, 5074-5085.